N-(ALPHA-ETHOXYALLYL)BENZOTRIAZOLE - A NOVEL PROPENOYL ANION SYNTHON ROUTE TO VINYL KETONES

被引：35

作者：

KATRITZKY, AR

ZHANG, GF

JIANG, JL

机构：

[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 23期

关键词：

D O I：

10.1021/jo00128a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation with butyllithium of N-(alpha-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, alpha,beta-unsaturated esters, alpha,beta-unsaturated ketones, and aldehydes gave exclusively alpha-alkylation adducts. These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.

引用

页码：7589 / 7596

页数：8

共 48 条

[1] REACTIONS OF ACYL ANION EQUIVALENTS DERIVED FROM CYANOHYDRINS, PROTECTED CYANOHYDRINS AND ALPHA-DIALKYLAMINONITRILES [J].